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New Aspects of Synthesis and Properties of Arylated Cyclopentadienes
Author(s) -
Dyker Gerald,
Heiermann Jörg,
Miura Masahiro
Publication year - 2003
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200303079
Subject(s) - cyclopentadiene , conformational isomerism , mesitylene , chemistry , steric effects , aryl , palladium , photochemistry , organic chemistry , molecule , catalysis , alkyl
The multifold palladium‐catalysed arylation is a suitable method for the synthesis of sterically crowded cyclopentadienes bearing up to five ortho ‐substituted aryl groups. A maximum of four mesitylene groups can be introduced. While penta( para ‐xylyl)cyclopentadiene and pentakis(2‐chlorophenyl)cyclopentadiene exhibit at least six rotamers in the proton NMR spectrum, only two rotamers are registered for the tetra(2‐chlorophenyl)cyclopentadiene; the all‐ trans isomer is identified as the major one both by spectroscopy and by semi‐empirical calculations.